During his time at Trinity College, he began to get noticed in bars and clubs, with a long term residency at The Dorchester hotel, London.[7]

Stilgoe's first public engagement was at the Pizza on the Park, London in 2004. Following the performance, Dame Cleo Laine later called Stilgoe in to perform with her and husband Sir John Dankworth on their Radio 2 show Live at the Stables.[7] He then signed with jazz label Candid in 2007, Candid released his debut album I Like This One in 2008 to praise from national press.[8]

After contractual issues with Candid, Stilgoe bought himself out of the contract and used money earned from his concerts to record demos of new songs. Nick Stewart then signed Stilgoe under his management with Nick Stewart and Associates in 2010.[11]

With Grammy-nominated producer James McMillan, Stilgoe recorded a new album We Look to the Stars, released in July 2012. The album went to number 1 in the Amazon Jazz Chart[12] on its day of release. From the album, We Should Kiss was released as a single in July 2012. The single was used by French shoe designer Christian Louboutin in his showcase –Fue at Le Crazy Horse in Paris and exhibition at the London Design Museum.,[13][14] In February 2014, Stilgoe released a live album Songs on Film, which includes songs from classic American films and Stilgoe's original compositions inspired by them.[15] The album was commercially released by Linn Records on 17 November 2014, alongside his earlier albums. Stilgoe has participated in numerous recording sessions as both a pianist and singer; including the single "Elephant" by Alexandra Burke.